Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe

A homocysteine ​​and glutathione technology, applied in chemical instruments and methods, fluorescence/phosphorescence, analytical materials, etc., can solve the problems of indistinguishable detection and achieve high yield and simple synthesis

Inactive Publication Date: 2017-04-26
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, although a large number of Cys / Hcy, GSH and H 2 S fluorescent probes, but they are not yet able to combine Cys / Hcy, GSH and H 2 S distinguishes and detects

Method used

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  • Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe
  • Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe
  • Fluorescent probe capable of separately detecting cysteine/homocysteine, glutathione and sulfuretted hydrogen and preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of compound 2:

[0036]

[0037] Place 175mg of oxindole (1.0mmol), 342mg (2.0mmol) of benzyl bromide and 232mg of potassium iodide (2.0mmol) in a round bottom flask, add acetonitrile to completely dissolve the reactant, heat the reaction solution to reflux, and stir for reaction 6 Hour. After the reaction was completed, the solvent was removed by rotary evaporator underpressure distillation to obtain a crude product, which was purified with a silica gel (200-300 mesh) chromatographic column with a volume ratio of 50:1 of dichloromethane and ethanol as the eluent. 252 mg of a dark brown solid were obtained (64% yield). 1 H NMR (400MHz, CD 3 OD), δ(ppm): 1.64(s, 6H), 5.77(s, 2H), 6.91-6.94(dd, J=8.8, 2.4Hz, 1H), 7.136-7.142(d, J=2.4Hz, 1H ), 7.37-7.38(2H), 7.42-7.48(3H), 7.56-7.58(d, J=8.8Hz, 1H); 13 C NMR (100MHz, CD 3 OD): δ(ppm): 14.61, 22.80, 51.04, 54.46, 111.01, 115.79, 117.43, 127.81, 129.15, 129.74, 132.73, 133.52, 144.61, 159.66, 197.29.

[00...

Embodiment 2

[0045] Probe HMN with different equivalents of Cys / Hcy, GSH and H 2 Fluorescence Spectrum Changes of S Reaction

[0046] The probe HMN prepared in Example 1 was dissolved in acetonitrile to make a concentration of 1.0mmol / L probe mother solution (the concentration of probe HMN was 1.0mmol / L); Cys / Hcy, GSH and H 2 S was added to distilled water to prepare Cys / Hcy, GSH and H at a concentration of 5 mmol / L. 2 S mother liquor. Take 30μL from the probe mother solution and add it to a 5mL centrifuge tube, and add different equivalents of Cys / Hcy, GSH (0-100eq) and H 2 S (0-500eq) mother liquor was diluted to 3mL with 0.57mL acetonitrile and different volumes of PBS aqueous solution (concentration 25mmol / L, pH 7.4), and configured as a test solution with a probe concentration of 10μmol / L and 20% acetonitrile. Test the probe with different equivalents of Cys / Hcy, GSH (0-100eq) and H with a fluorescence spectrometer 2 Fluorescence spectrum changes of S (0-500eq) reaction solution (...

Embodiment 3

[0048] Probe HMN and Cys / Hcy, GSH and H 2 Fluorescence change of S over time

[0049] Take 30 μL from the mother solution of the probe in Example 2 and add it to a 5mL centrifuge tube, and add different equivalents of Cys / Hcy (55eq), GSH (65eq) and H 2 S (50 or 500eq) mother solution was diluted to 3mL with 0.57mL acetonitrile and different volumes of PBS aqueous solution (concentration 25mmol / L, pH 7.4), and configured as a test solution with a probe concentration of 10μmol / L and 20% acetonitrile. Using excitation wavelengths of 410, 470 and 550 nm, respectively, the fluorescence spectra of the probes as a function of time were tested. Depend on Figure 8 It can be seen that with the increase of time, after adding Cys / Hcy, the fluorescence intensity at 485 and 609nm gradually increased, and reached the maximum at about 12 / 20 and 15 / 20min respectively; after adding GSH, the fluorescence intensity at 609nm Gradually become larger and reach the maximum value at about 20min; a...

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PUM

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Abstract

The invention discloses a fluorescent probe capable of separately detecting cysteine / homocysteine, glutathione and sulfuretted hydrogen and a preparation method and application of the fluorescent probe. The molecular formula of the probe is C38H28IN5O5S, and the structural formula is shown in the description. The probe is simple to synthesize, higher in yield, can separately detect Cys / Hcy, GSH and H2S in a water solution, and can separately detect Cys / Hcy, GSH and H2S in the living cell level.

Description

technical field [0001] The invention relates to a fluorescent probe for distinguishing and detecting cysteine / homocysteine, glutathione and hydrogen sulfide based on a multi-signal mode, a preparation method and an application thereof, and belongs to the technical field of analytical chemistry. Background technique [0002] Reactive sulfur species (RSS), including small molecular biothiols (Thiols) and gaseous molecular hydrogen sulfide (H 2 S), is a class of biologically active molecules that play an important physiological role in the human body. Cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) are the three most common small molecule biothiols, however, they have distinct biological and pharmacological effects and interact with each other at the same time. There is also a close relationship between them. Cys is the precursor of acetyl coenzyme, taurine and GSH, and can also form sulfur-iron complexes with iron ions, but abnormal levels of Cys usually cause s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1048G01N21/6486
Inventor 林伟英何隆薇杨雪玲徐凯欣
Owner UNIV OF JINAN
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